CA2546387A1 - Derives de phenylpyridinylpiperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent - Google Patents
Derives de phenylpyridinylpiperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent Download PDFInfo
- Publication number
- CA2546387A1 CA2546387A1 CA002546387A CA2546387A CA2546387A1 CA 2546387 A1 CA2546387 A1 CA 2546387A1 CA 002546387 A CA002546387 A CA 002546387A CA 2546387 A CA2546387 A CA 2546387A CA 2546387 A1 CA2546387 A1 CA 2546387A1
- Authority
- CA
- Canada
- Prior art keywords
- branched
- linear
- formula
- alkyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 4
- JLECMXGHGHVRFB-UHFFFAOYSA-N 2-phenyl-1-pyridin-2-ylpiperazine Chemical class C1NCCN(C=2N=CC=CC=2)C1C1=CC=CC=C1 JLECMXGHGHVRFB-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract 4
- 229940079593 drug Drugs 0.000 claims abstract 4
- -1 carboxy, hydroxy Chemical group 0.000 claims description 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
- 230000032683 aging Effects 0.000 claims description 6
- 230000006735 deficit Effects 0.000 claims description 6
- 230000000742 histaminergic effect Effects 0.000 claims description 6
- 230000002490 cerebral effect Effects 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
- 208000019022 Mood disease Diseases 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 208000013403 hyperactivity Diseases 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 206010010904 Convulsion Diseases 0.000 claims description 3
- 208000006264 Korsakoff syndrome Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000005557 antagonist Substances 0.000 claims description 3
- 230000007278 cognition impairment Effects 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- TWGISPYSLQTLNK-UHFFFAOYSA-N n-[4-[6-(4-cyclopentylpiperazin-1-yl)pyridin-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CC=C(N2CCN(CC2)C2CCCC2)N=C1 TWGISPYSLQTLNK-UHFFFAOYSA-N 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 230000002739 subcortical effect Effects 0.000 claims description 3
- 230000002792 vascular Effects 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 2
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 230000008018 melting Effects 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 15
- 238000004452 microanalysis Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 210000004556 brain Anatomy 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229960001340 histamine Drugs 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- FHQDWPCFSJMNCT-UHFFFAOYSA-N N(tele)-methylhistamine Chemical compound CN1C=NC(CCN)=C1 FHQDWPCFSJMNCT-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WHKWMTXTYKVFLK-UHFFFAOYSA-N 1-propan-2-ylpiperazine Chemical compound CC(C)N1CCNCC1 WHKWMTXTYKVFLK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 102000000543 Histamine Receptors Human genes 0.000 description 3
- 108010002059 Histamine Receptors Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000006196 drop Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000007171 neuropathology Effects 0.000 description 3
- 239000002858 neurotransmitter agent Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- VLVCDUSVTXIWGW-UHFFFAOYSA-N 4-iodoaniline Chemical compound NC1=CC=C(I)C=C1 VLVCDUSVTXIWGW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 230000002920 convulsive effect Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 230000020595 eating behavior Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000013016 learning Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- LTSCPIBHEJPMSC-UHFFFAOYSA-N n-[4-[6-(4-propan-2-ylpiperazin-1-yl)pyridin-3-yl]phenyl]benzenesulfonamide;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C1=CC=C(C=2C=CC(NS(=O)(=O)C=3C=CC=CC=3)=CC=2)C=N1 LTSCPIBHEJPMSC-UHFFFAOYSA-N 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000003518 presynaptic effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000033764 rhythmic process Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PVMCQBPJKPMOKM-UHFFFAOYSA-N 1-cyclopentylpiperazine Chemical compound C1CCCC1N1CCNCC1 PVMCQBPJKPMOKM-UHFFFAOYSA-N 0.000 description 1
- HNZJIWIXRPBFAN-UHFFFAOYSA-N 1-cyclopropylpiperazine Chemical compound C1CC1N1CCNCC1 HNZJIWIXRPBFAN-UHFFFAOYSA-N 0.000 description 1
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KHOITXIGCFIULA-UHFFFAOYSA-N Alophen Chemical compound C1=CC(OC(=O)C)=CC=C1C(C=1N=CC=CC=1)C1=CC=C(OC(C)=O)C=C1 KHOITXIGCFIULA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102000007527 Autoreceptors Human genes 0.000 description 1
- 108010071131 Autoreceptors Proteins 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 238000001061 Dunnett's test Methods 0.000 description 1
- 102000004384 Histamine H3 receptors Human genes 0.000 description 1
- 108090000981 Histamine H3 receptors Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- 108090000189 Neuropeptides Proteins 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000002903 catalepsic effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000002060 circadian Effects 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000008713 feedback mechanism Effects 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229940049906 glutamate Drugs 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000006386 memory function Effects 0.000 description 1
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KXIBCCFSAMRWIC-UHFFFAOYSA-N morpholine-4-sulfonyl chloride Chemical compound ClS(=O)(=O)N1CCOCC1 KXIBCCFSAMRWIC-UHFFFAOYSA-N 0.000 description 1
- IXLQQINBCDIZGZ-UHFFFAOYSA-N n-(4-iodophenyl)benzenesulfonamide Chemical compound C1=CC(I)=CC=C1NS(=O)(=O)C1=CC=CC=C1 IXLQQINBCDIZGZ-UHFFFAOYSA-N 0.000 description 1
- SREMDYGUGILBIV-UHFFFAOYSA-N n-(4-iodophenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(I)C=C1 SREMDYGUGILBIV-UHFFFAOYSA-N 0.000 description 1
- AKPZQATZUULYPZ-UHFFFAOYSA-N n-(4-iodophenyl)morpholine-4-sulfonamide Chemical compound C1=CC(I)=CC=C1NS(=O)(=O)N1CCOCC1 AKPZQATZUULYPZ-UHFFFAOYSA-N 0.000 description 1
- KPQBYAHHOYPQMQ-UHFFFAOYSA-N n-(4-iodophenyl)propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NC1=CC=C(I)C=C1 KPQBYAHHOYPQMQ-UHFFFAOYSA-N 0.000 description 1
- RGUJJINDBXNBSY-UHFFFAOYSA-N n-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzenesulfonamide Chemical compound O1C(C)(C)C(C)(C)OB1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC=C1 RGUJJINDBXNBSY-UHFFFAOYSA-N 0.000 description 1
- NPSPNWPZDXQYAC-UHFFFAOYSA-N n-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(NS(C)(=O)=O)C=C1 NPSPNWPZDXQYAC-UHFFFAOYSA-N 0.000 description 1
- HTRQAKVQAAGOMU-UHFFFAOYSA-N n-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine-4-sulfonamide Chemical compound O1C(C)(C)C(C)(C)OB1C(C=C1)=CC=C1NS(=O)(=O)N1CCOCC1 HTRQAKVQAAGOMU-UHFFFAOYSA-N 0.000 description 1
- DIHPCBICXLFFQP-UHFFFAOYSA-N n-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 DIHPCBICXLFFQP-UHFFFAOYSA-N 0.000 description 1
- XQCVNILPBPGGDZ-UHFFFAOYSA-N n-[4-[6-(4-cyclopentylpiperazin-1-yl)pyridin-3-yl]phenyl]benzenesulfonamide;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1S(=O)(=O)NC(C=C1)=CC=C1C(C=N1)=CC=C1N(CC1)CCN1C1CCCC1 XQCVNILPBPGGDZ-UHFFFAOYSA-N 0.000 description 1
- YGLQQIJCMOZMSQ-UHFFFAOYSA-N n-[4-[6-(4-propan-2-ylpiperazin-1-yl)pyridin-3-yl]phenyl]morpholine-4-sulfonamide;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C1=CC=C(C=2C=CC(NS(=O)(=O)N3CCOCC3)=CC=2)C=N1 YGLQQIJCMOZMSQ-UHFFFAOYSA-N 0.000 description 1
- IKIBZVKXCTTZLK-UHFFFAOYSA-N n-[4-[6-(4-propan-2-ylpiperazin-1-yl)pyridin-3-yl]phenyl]propane-2-sulfonamide;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C1=CC=C(C=2C=CC(NS(=O)(=O)C(C)C)=CC=2)C=N1 IKIBZVKXCTTZLK-UHFFFAOYSA-N 0.000 description 1
- 230000000955 neuroendocrine Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000001962 neuropharmacologic effect Effects 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000000803 paradoxical effect Effects 0.000 description 1
- 230000001936 parietal effect Effects 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- ZRHANBBTXQZFSP-UHFFFAOYSA-M potassium;4-amino-3,5,6-trichloropyridine-2-carboxylate Chemical compound [K+].NC1=C(Cl)C(Cl)=NC(C([O-])=O)=C1Cl ZRHANBBTXQZFSP-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000003956 synaptic plasticity Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000028016 temperature homeostasis Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0504757A FR2885615B1 (fr) | 2005-05-12 | 2005-05-12 | Nouveaux derives de phenylpyridinylpiperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
FR05/04757 | 2005-05-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2546387A1 true CA2546387A1 (fr) | 2006-11-12 |
Family
ID=35677562
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002546387A Abandoned CA2546387A1 (fr) | 2005-05-12 | 2006-05-12 | Derives de phenylpyridinylpiperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Country Status (21)
Country | Link |
---|---|
US (1) | US7494995B2 (xx) |
EP (1) | EP1721896A1 (xx) |
JP (1) | JP2006342158A (xx) |
KR (1) | KR100807482B1 (xx) |
CN (1) | CN100540536C (xx) |
AR (1) | AR054120A1 (xx) |
AU (1) | AU2006201993A1 (xx) |
BR (1) | BRPI0601725A (xx) |
CA (1) | CA2546387A1 (xx) |
EA (1) | EA011165B1 (xx) |
FR (1) | FR2885615B1 (xx) |
GE (1) | GEP20084503B (xx) |
HK (1) | HK1096097A1 (xx) |
MA (1) | MA28325A1 (xx) |
MY (1) | MY140963A (xx) |
NO (1) | NO20062100L (xx) |
NZ (1) | NZ547121A (xx) |
SG (1) | SG127800A1 (xx) |
UA (1) | UA87283C2 (xx) |
WO (1) | WO2006120348A1 (xx) |
ZA (1) | ZA200603809B (xx) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030236259A1 (en) * | 2002-02-05 | 2003-12-25 | Rolf Hohlweg | Novel aryl- and heteroarylpiperazines |
CA2614116A1 (en) | 2005-07-04 | 2007-01-11 | Novo Nordisk A/S | Novel medicaments |
CN102295606A (zh) * | 2006-05-29 | 2011-12-28 | 高点制药有限责任公司 | 合成3-(1,3-苯并间二氧杂环戊烯-5-基)-6-(4-环丙基哌嗪-1-基)-哒嗪的方法及其适用的中间体 |
EP2014656A3 (en) | 2007-06-11 | 2011-08-24 | High Point Pharmaceuticals, LLC | New heteocyclic h3 antagonists |
EP2598481B1 (en) | 2010-07-26 | 2016-08-31 | Bristol-Myers Squibb Company | Sulfonamide compounds useful as cyp17 inhibitors |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0361489A3 (en) * | 1988-09-30 | 1991-06-12 | Chugai Seiyaku Kabushiki Kaisha | Novel 3,4-diaminoquinoline and pyridine compounds |
JP2563402Y2 (ja) * | 1989-09-28 | 1998-02-25 | 株式会社小松製作所 | ディーゼルエンジンのピストン |
WO1992005156A1 (en) * | 1990-09-13 | 1992-04-02 | Smithkline Beecham Corporation | Pyridylthio or pyridyloxy alkanoic acids |
CN1088459C (zh) * | 1996-10-04 | 2002-07-31 | 诺沃挪第克公司 | 1,4-二取代的哌嗪 |
ATE404539T1 (de) * | 1997-10-02 | 2008-08-15 | Eisai R&D Man Co Ltd | Kondensierte pyridinderivate |
WO1999021834A1 (en) * | 1997-10-27 | 1999-05-06 | Neurosearch A/S | Heteroaryl diazacycloalkanes as cholinergic ligands at nicotinic acetylcholine receptors |
GB9919776D0 (en) * | 1998-08-31 | 1999-10-27 | Zeneca Ltd | Compoujnds |
US20030236259A1 (en) * | 2002-02-05 | 2003-12-25 | Rolf Hohlweg | Novel aryl- and heteroarylpiperazines |
-
2005
- 2005-05-12 FR FR0504757A patent/FR2885615B1/fr not_active Expired - Fee Related
-
2006
- 2006-05-02 MA MA28996A patent/MA28325A1/fr unknown
- 2006-05-05 SG SG200603043A patent/SG127800A1/en unknown
- 2006-05-10 MY MYPI20062153A patent/MY140963A/en unknown
- 2006-05-10 NO NO20062100A patent/NO20062100L/no not_active Application Discontinuation
- 2006-05-11 US US11/432,787 patent/US7494995B2/en not_active Expired - Fee Related
- 2006-05-11 AR ARP060101888A patent/AR054120A1/es unknown
- 2006-05-11 GE GEAP20069392A patent/GEP20084503B/en unknown
- 2006-05-11 WO PCT/FR2006/001049 patent/WO2006120348A1/fr active Application Filing
- 2006-05-11 NZ NZ547121A patent/NZ547121A/en unknown
- 2006-05-11 EP EP06290757A patent/EP1721896A1/fr not_active Withdrawn
- 2006-05-11 UA UAA200605181A patent/UA87283C2/ru unknown
- 2006-05-12 CA CA002546387A patent/CA2546387A1/fr not_active Abandoned
- 2006-05-12 AU AU2006201993A patent/AU2006201993A1/en not_active Abandoned
- 2006-05-12 EA EA200600761A patent/EA011165B1/ru not_active IP Right Cessation
- 2006-05-12 KR KR1020060042827A patent/KR100807482B1/ko not_active IP Right Cessation
- 2006-05-12 BR BRPI0601725-8A patent/BRPI0601725A/pt not_active IP Right Cessation
- 2006-05-12 CN CNB2006101263974A patent/CN100540536C/zh not_active Expired - Fee Related
- 2006-05-12 JP JP2006133321A patent/JP2006342158A/ja active Pending
- 2006-05-12 ZA ZA200603809A patent/ZA200603809B/xx unknown
-
2007
- 2007-03-30 HK HK07103457.3A patent/HK1096097A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
GEP20084503B (en) | 2008-10-10 |
HK1096097A1 (en) | 2007-05-25 |
US20060258671A1 (en) | 2006-11-16 |
US7494995B2 (en) | 2009-02-24 |
ZA200603809B (en) | 2007-08-29 |
EA200600761A1 (ru) | 2006-12-29 |
MY140963A (en) | 2010-02-12 |
MA28325A1 (fr) | 2006-12-01 |
FR2885615A1 (fr) | 2006-11-17 |
FR2885615B1 (fr) | 2007-06-22 |
JP2006342158A (ja) | 2006-12-21 |
AR054120A1 (es) | 2007-06-06 |
WO2006120348A1 (fr) | 2006-11-16 |
SG127800A1 (en) | 2006-12-29 |
AU2006201993A1 (en) | 2006-11-30 |
CN100540536C (zh) | 2009-09-16 |
KR100807482B1 (ko) | 2008-02-25 |
UA87283C2 (ru) | 2009-07-10 |
CN1896062A (zh) | 2007-01-17 |
NZ547121A (en) | 2007-05-31 |
EP1721896A1 (fr) | 2006-11-15 |
KR20060117262A (ko) | 2006-11-16 |
BRPI0601725A (pt) | 2007-05-08 |
EA011165B1 (ru) | 2009-02-27 |
NO20062100L (no) | 2006-11-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2555216C (fr) | Nouveaux derives azabicycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
EP1721897A1 (fr) | Dérivés de phénylpyridinylpipérazine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
CA2546387A1 (fr) | Derives de phenylpyridinylpiperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
CA2351833C (fr) | Nouveaux composes cyclopropaniques, 1,1 et 1,2-disubstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
EP1669072A1 (fr) | Dérivés de benzothiazine et benzothiadiazine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
EP1757586B1 (fr) | Nouveaux composés 1,1-pyridinylaminocyclopropanamines polysubstitués, leur procédé de préparation et les compositions pharmaceutiques yui les contiennent | |
FR2953515A1 (fr) | Nouveaux derives du type hexahydrocyclopenta[b]pyrrole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
EP1176148A1 (fr) | Nouveaux dérivés de benzothiadiazine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
CA2668527A1 (fr) | Nouveaux derives azabicycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
CA2782469C (fr) | Derives azabicyclo [3.1.0] hex- 2 -yl, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
CA2552827A1 (fr) | Composes 1-1-pyridinyloxycyclopropanamines polysubstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
EP2332910B1 (fr) | Nouveaux dérivés azabicyclo[3.2.0] hept-3-yl, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
WO2009106753A1 (fr) | Nouveaux derives d'1h-indol-1-yl uree, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
MXPA06005180A (en) | Novel phenyl-pyridinyl-piperazine derivatives, a method for the production thereof and pharmaceutical compositions containing said derivatives | |
FR2953513A1 (fr) | Nouveaux derives azabicyclo[3.2.0]hept-6-yl, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
FR2819253A1 (fr) | Nouveaux derives d'acide hydroxamique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Discontinued |